Water → HCID 86702587, compound

HRID 1746819Notes

Reaction equation

HRID 1746819 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:11]2[C@@H:6]([S:7][C@@H:8]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:9][CH2:10]2)[CH2:5][C@H:4]1[O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1.C(N(C(C)C)CC)(C)C.N1C=CC=CC=1.S(=O)(=O)=O.O>C(OCC)(=O)C.CS(C)=O>[CH:2]([C@@H:3]1[C@@H:11]2[C@@H:6]([S:7][C@@H:8]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:9][CH2:10]2)[CH2:5][C@H:4]1[O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)=[O:1]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 168533Sulfur trioxide-pyridineHCID 86702585HCID 86702585, compound

Product 1

HCID 86702587HCID 86702587, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound 10 (200 mg) was dissolved in ethyl acetate (1.7 mL) and dimethyl sulfoxide (0.84 mL), diisopropylethylamine (0.39 mL) was added, and the mixture was cooled in an ice bath. Sulfur trioxide-pyridine (256 mg) was added, and the mixture was stirred for 10 minutes, then poured into water, and extracted with ethyl acetate. The organic layer was washed with water and a saturated saline, dried with anhydrous magnesium sulfate, and then concentrated to obtain a titled compound (200 mg) having the following physical property values.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated saline, dried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-12890794ed8944b0b64774f78853c40f
Source dataset
uspto-grants-2015_10
Patent number
US09150537B2

Reaction notes

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